Question about Support request etiquette and frequency

So, about a month ago I reported someone because I noticed that they regifted something. Today I noticed that the same person regifted something yet again. Should I report this person again with a separate request, add something to the first request, or neither? Should they just already be on support's radar now? I somewhat think the person simply doesn't understand the rules, so I thought about talking to the user, but if they are intentionally breaking the rules, it's really not a confrontation I would look forward to having (I prefer to leave things up to the authorities and retain my shiny, happy version of SG).

Any suggestions?

EDIT: I wanted to clarify that I basically do not want to annoy the support members if it isn't necessary, since they're awesome and I know policing this site (And STrades for any that do both) is probably incredibly taxing.

(also several edits because I can't spell right after waking up)